A Strange Cuckolding
Copyright© 2025 by jack tar
Chapter 1
BDSM Sex Story: Chapter 1 - This is a story from a work friend, he has told it to me, and so I have presented it as if he were telling you. He found himself submissive to a much older man who then makes him help coerce his wife to sexually submit to him too.
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa Ma/Ma Coercion Consensual Drunk/Drugged Gay BiSexual Heterosexual Cuckold Wife Watching Wimp Husband DomSub MaleDom Humiliation Rough Anal Sex Cream Pie Exhibitionism First Masturbation Oral Sex Petting Voyeurism Size
I always thought of myself as an average guy. Married for over several years with two children. The last of which is now moved out and away. I’m not sure when exactly that I started to feel that I was curious about other men. Maybe curious is the wrong word to use. I don’t really like men. I prefer women, but I get something from men that I don’t get from women. I discovered that I enjoyed being a submissive and treated poorly by a dominant man. I realised I like to be used.
I started looking for ads for men when I discovered Terry’s ad. He invited me to his place. I was very nervous and was a little surprised when I showed up. Not only was he quite a bit older than my 30years (I would guess him to be about 65, which I later confirmed to be true) but he was quite small and thin and wiry. Maybe weighing in at 110 pounds. Missing a couple of his front teeth also made him less than intimidating standing against my 180pound 6 foot frame.
I sat down on his couch and he asked what exactly I wanted from him. I told him I didn’t exactly know, but I knew that I wanted to try being with a guy for the first time. I wanted to be used, however he saw fit for his own pleasure. He said that would be acceptable and he would test my limits. However, once we started, he was in charge. I agreed. So here I am being taken over by this frail old man, 30+ years my senior and half my size.
Without any more small talk, he told me to get down on my knees and pull down his gym shorts. I eagerly complied. Surprisingly, out popped and very large semi-rigid penis maybe 8 inches in length. He grabbed it with one hand and my head with the other and promptly started to jam it in my mouth, telling me to “Open up, you little bitch.” I complied and found myself eagerly sucking on his expanding cock in an attempt to deep throat it all the while gagging on it. He was quite vocal with me and, after a few minutes, demanded me to strip naked while he smeared some sort of lube over his cock. I never hesitated to listen and even found myself saying, “Yes sir. Please use me.”
He ordered me to bend over the end of his couch and then started to rub his engorged cock along my hole, all the while dripping more lube on it. And then he pushed in. It felt hard and hurt like hell. When I tried to complain, he smacked my ass and said sissies get what they need and that I was to shut up. He continued to work it inside my hole until he had me impaled and then started sawing that magnificent cock in and out of my ass, all the while smacking me and degrading me.
Terry told me that he was daddy now and I was just a useless slut with a hole for him to use. He pounded me mercilessly for several minutes until he came inside me and then promptly collapsed on top of me, panting loudly. He pulled out of my ass and then told me to get out. He would message when he needed me again.
I left feeling sore and very used, but also happy that I could please this old man who lived alone and with no one to look after him. He would call on me once every week or two and would often put a leash on me and make me crawl and beg for his cock. He referred to it as his slug. It was huge, thick, and slimy and left a trail, but never truly hard but still it filled me. He made me tell him things about my personal life and even show him pictures of my wife. He would ask me how such a pathetic little sissy could please a woman, even to the point of saying that she needs a real man in her life. This placed thoughts in my head that I hadn’t entertained before. It made me hard.
Several months went by and Terry forced me to provide many pictures of my wife. As well as many details of our life. He became interested in her and it was making me nervous. I could feel it in my gut. I was scared, but also excited. I couldn’t refuse him.
One day Terry finished fucking me missionary style. He loved being on top and he came hard inside of me while my little cock just flopped about. All the while, he was calling me by her name and made me pretend to be her. I had to say things like “Put a baby in me” or “You’re so big ... much bigger than my little husband.” Afterwards, while I was dressing, he told me he wanted her and was going to bed her with my help. I was shocked and at the same time so excited that my cock got hard instantly and he just laughed. Calling me pathetic and told me to get out.
For quite some time, he kept after me going on about her. He told me I had to introduce them. He had a plan.
So here I am with my wife of over twenty years out grocery shopping. And here comes Terry waving at me and saying hi while my wife is curious as to who he is. I introduce him as an old co-worker friend who had retired some years earlier. My wife thought he was a funny old man and completely harmless. She invited him for dinner so we could catch up that very same night. Little did she know what that would bring about?
Several hours later, we were sitting at the dinner table finishing off a bottle of wine Terry had brought along. My wife was wearing one of her favourite sundresses that showed just a hint of cleavage and a lot of leg sitting a few inches above the knee. She was beautiful, with her shoulder-length blonde hair tied back in a ponytail.
After some small talk and opening another bottle of wine, Terry excused himself to use the washroom. My wife took this as a chance to clear of some of the dinnerware from the table. Terry returned and then picked up a couple of plates and went into the kitchen. After several minutes, I entered the kitchen to the sound of clanging dishes where my wife and Terry were hard at work washing them. He winked at me. She looked a little flushed.
Terry left not long afterwards. We watched a little television to wind down before bed and while I massaged her feet. I asked her what she thought of old-man Terry. After a moment, she said that he was nice and was happy to entertain him so we could catch up, but that he was too old for us to have as a close friend. I thought that last statement weird, but she wouldn’t elaborate on it and I let it drop.